Warning: This story features bondage.

Context: This is a short story written for Day 21 of Kinktober 2025 using the prompt words Jail and Warden.

SLAM!

I smacked my baton down hard against the surface of the metal table, making Connie practically jump out of her skin. She hadn’t heard me enter the break room.

“Connie what the hell is this? You know you’re not allowed to smoke in here.”

Connie spluttered as she pulled her head in from the open window. She’d been sneaking in a cigarette break despite the prison having rules against smoking while on duty, especially indoors.

“S... sorry warden.”

“Why are you wasting time in the lounge room anyway? Patrol the blocks!”

“I did that just half an hour ago though.”

“Including Block D?”

“Well... ok not that one.”

I facepalmed. It was always the more junior guards getting so easily intimidated by Block D on the night shift. I knew I had a reputation for being a hard-ass, but it was clearly needed to toughen the staff up.

“Fine, I’ll do the patrol. The quarterly inventory of the storage shed is due soon. Go do that.”

“But-”

She cut herself off on seeing the unimpressed look on my face.

“Yes ma’am...”

I marched out of the room to head down towards Block D. Connie hung back and when she was sure I wasn’t going to immediately return, lit up another cigarette.

“Screw you warden.”

My footsteps echoed across the large open space of cell block D. I strolled leisurely past the iron bars of so many cells. Several sleeping women stirred and looked up groggily as I passed, grumbling at the disturbance to their rest.

I was in charge of a women’s prison. Block D housed many of the rowdier and more violent criminals, hence many guards’ hesitance in going there. I had no such qualms, and readily dished out punishments whenever I felt discipline was slipping.

As I passed a particular cell, a shape lunged towards me from the darkness behind the bars.

“Boo!”

“AHH!”

I recoiled, almost tripping over. The figure that scared me neared the bars, grinning in the dimmed light.

She wore the prisoner uniform’s orange trousers and only a white bra as a top, revealing muscular arms and multiple prominent tattoos. Despite her tough-girl physique, her short dark hair and soft facial features were much more feminine. She would have been a real beauty if she hadn’t adopted the overall guise of a thug.

“Why if it isn’t our dear warden. What has you out doing grunt work this late? Don’t tell me, you came to see little old me? I’m flattered.”

Roxanne. Possibly my least favourite inmate in the whole place. She’d been convicted of sex trafficking, but I suspected she was guilty of much more. In her one year imprisoned she’d already become the ringleader of the biggest prison gang.

“Get your ass back in bed Roxanne.”

“If I don’t will you make me? You can join me in it~”

I stepped closer.

“If you’re not lying facedown on that mattress in ten seconds, I’ll make sure you regret it for a long ti-”

Like a flash, she’d dashed forward and reached an arm through the bars. She grasped the centre of my white buttoned shirt, yanking me in, making me slam hard against the metal. Her other arm laced through and around the back of my neck, holding my head in, making my face squash between the vertical gap between poles.

She leaned in and planted kisses on my face and lips. I tried to pull back but her arms were like a vice, holding me rock steady.

“Mwah, mwah, mmmwah! You’re so pretty warden~. You should give up the act and take your true place at my feet.”

While she was groping my chest, I managed to steady the baton and shift aside enough to create a target. I thrust it tip-first through the bars, striking Roxanne in the stomach. She gasped and released me, stumbling back winded.

“Y... you b... bitch...”

“Y-you think you can do that to me? You can look forward to a week in solitary. Maybe that’ll set you straight.”

She glared at me with unbridled fury. It was enough to send a shiver down my spine. I was glad to be on the other side of her cage. Enough patrolling. Time to head back to the main block.

BWAM! BWAM! BWAM! BWAM!

I almost jumped in shock as an alarm blasted out of nowhere.

fsss! fss! fsssssss!

A second later, all of the fire sprinklers activated, dousing the whole place in a fine mist of water. My wet shirt went see-through, clinging against me.

Why had the fire alarm been set off? Was it an error? What could possibly have caused it?

The obvious answer came to me. Connie. It had to be. She’d disobeyed my orders and smoked indoors. Again! This time accidentally triggering the smoke detector. Oh I was going to make her badly regret that once I got back to-

clank! .... clank! clank! clank!

One after another, heavy metallic noises sounded out, starting farther down the block and travelling closer. I suddenly remembered part of the protocol when there was a fire, one intended for the safety of all the inmates.

With dread in my gut, I saw women in orange jumpsuits step forward out of their cells. All the doors had automatically unlooked. Several of the nearer girls started approaching.

“S-stay back!”

I waved my baton wildly, backing away. I didn’t have long before everyone was awake. I needed to get to--

A hand grabbed my arm, twisting it down painfully, forcing me to drop the baton. Roxanne pulled me close and whispered in my ear.

“What was that about solitary confinement warden? I think it's you who's due some punishment.”

I whimpered as she twisted my arm further and licked my cheek.

Connie took a lazy drag of her cigarette, head out the window, blinking in the afternoon sun. As the break room door opened, she scrambled to hide it quickly.

“I was just um...”

“Don’t worry your head honey. I’m the new warden. Nice to meetcha~”

“Ah! Hello.”

Connie shook the stocky woman's hand. She had a wide cheerful grin, the exact opposite of the previous warden who’d been missing ever since the fire alarm incident two weeks ago.

“I don’t suppose you know anything about what happened to...”

“My predecessor? Nah. The official position is that Warden Stevens abandoned her duty and went into hiding because she expected to be fired and potentially prosecuted over that incident. Good riddance to her. I bet you had a hell of a night trying to wrangle that mess she made.”

“Uhh yeah... that she made... Yeah it was a tough night. The prisoners were all over the place, but we kept the outer gate locked and got everything under control by the morning.”

Connie tried to palm the cigarette as she began walking past.

“Sooo I suppose I should get on with doing the storage shed inventory. The quarterly check is overdue...”

“Actually I was wondering if I could bum a smoke off you?"

“Y-you saw that? So it’s not a problem for me to take a smoking break...?”

“Problem?! Heck take all you like. And let’s mark that storage inventory thing as completed and leave it for next year eh~?” wink

“Really? Awesome!”

Connie felt like a weight was lifted. This new warden was going to be a lot more pleasant to work under.

The prisoners all spread out into the yard for their extended unsupervised exercise period. The new management was a lot more lax than the old one.

Roxanne and two lackeys strolled to the far corner, where there was a keypad-locked gate to another fenced area. Roxanne swiped a card labelled [Warden Stevens] through the reader and the door clicked open.

They continued through the empty unmonitored section to a large shed at the back. The two lackeys stood guard as Roxanna entered alone. Inside there were spare mattresses piled high and various other equipment. Roxanne shoved one of the mattress piles aside a few feet and slipped through the gap.

From the floor of my small hidden area behind the stacks, I looked up at Roxanne.

“Mmmmph...”

“Morning my sweet little prisoner. Aww are you feeling a little stiff after how I left you?”

I was held in a ball-tie and lying on my side, with my knees folded up and my wrists and elbows bound together behind me. Roxanne sat me upright and removed the cord connecting my neck to my knees, allowing me to stretch my legs out.

I’d been restricted by a variety of makeshift restraints – torn bedsheets, belts, jump-ropes – as well as some smuggled-in contraband. In particular a large black ballgag had me whimpering and drooling all night long.

Roxanne unstrapped the gag and pulled it off, then gently reached inside my mouth and slowly pulled out a crumpled-up piece of cloth that had been tucked behind the ballgag. I coughed as I was finally rid of the unsavoury stuffing.

“How were Minnie’s panties? Not to your liking? Maybe Eve’s will be better~”

She held up a pair of black bloomers which had a suspicious light stain at the crotch.

“You’ll be sucking on these once we’re done. Eve ‘prepared’ them especially for you last night. We negotiated a trade of goods and part of our end is making sure you spend a week choking on her used panties. It’s funny isn’t it? All those pointless gang fights and divisions, and it was all solved by one thing we have in common: how much we all hate you.”

“R... Roxanne... p... please....”

SPANK!!

“Aaah!!”

“Did I say you could speak prisoner? I only want one thing from your mouth. You’ll get your meal soon enough, but first I want some sugar~”

She sat down in front of me and pulled me up, holding me close with her powerful arms.

“No I d-don’t... mmmhhh!!”

Her lips locked onto mine, and her tongue plunged into my mouth. She greedily kissed me and groped my ass while she did. I meekly kissed her back, knowing the rest of our ‘session’ together would go easier for me if I did. I tried not to think about how I was once the authority figure who kept her in line.

“Aaahh~. That’s a good prisoner. As a treat, I have two new presents for you!”

She fished inside the bag she’d brought with her. How did she keep sneaking these items into the prison? If I was still running things, none of it would have slipped by. I was stuck in this shed suffering from the incompetence of the new administration. Why hadn’t they done the inventory yet? They should have found me by now!

Roxanne pulled out a flimsy pink see-through dress. My jaw dropped. I was normally left wearing either a prisoner’s orange jumpsuit or just my underwear, but this was so much more humiliating.

I... I’m the warden. I’m supposed to be in charge! This is undignified!

“I think my little prisoner will look very tasty indeed in this~”

“N... no, I won’t! You need to release me now!!”

SPANK! SPANK!

“Ahhh! Wait, no... I’m sorry I’m sorry. Don’t- Mmmph!”

Roxanne had a threatening glare on her face as she shoved the ballgag back into my mouth.

“Maybe your second gift will help remind you of your place.”

The second object was an odd arrangement of black straps. I didn’t understand exactly what it was, until Roxanne stepped into it and pulled it up to her waist. A long thick black protrusion was sticking out from the front.

“Mmph? ... Mmmmh! MMMMPH!!!”

I moaned and thrashed hopelessly as Roxanne pushed me down onto my front, pulled down my panties, and positioned herself above me.

“Ready warden? Time to see what my penal code feels like~”

“MMMMH!!”